Corporate sponsorship is growing in importance as a form of marketing communication. The role of sponsorship is particularly relevant to bridge the gap between a wide range of publics and the corporate image. This work intends to narrow that gap. Through case studies the research identifies the difficulties companies face in selecting projects to receive sponsorship. Data were gathered through interviews with experts with experience with that process. Results suggest that problems are generated by two major factors: Professionals both from arts business and from the sponsoring companies seem unprepared for dealing with the process altogether. In addition, communication between both parts are rather cumbersome. As it shows the major obstacles to an efficient approach to the problem, this study subsidizes not only more immediate solutions but future studies on the subject.